Triethylamine → Ether methanol ammonium hydroxide

Participants

Reaction Conditions

Reaction Steps

To a solution of compound (AFD) (0.40 mmol) in dry DMF was added triethylamine (0.45), followed by the alkylating agent Br(CH2)2NHSO2CH3 (0.45 mmol). The resulting mixture was stirred at 80° C. overnight. After completion of the reaction, the cooled mixture was poured into 1M NaOH (150 mL) and extracted with ethyl acetate (2×100 mL). The organic extracts were dried (MgSO4) and the solvent evaporated at the rotary evaporator to leave a gum. Flash chromatography of the residue (SiO2, ether:methanol:ammonium hydroxide (200:10:1)) provided compound (AFV) as a colorless gum: (yield:26%); purity >97% (HPLC); MS: m/z 616.3 (M+1); 1H NMR (DMSO d6): δ 2.1–2.2 (br s, 3H), 2.3–2.4 (m, 5H), 2.75 (s, 3H) 2.9–2.10 (br s, 3H), 3.3–3.4 (m, 6H), 3.5 (m, 3H), 4.65 (m, 2H), 7.15–7.5 (m, 16H).

Provenance & Evidence